1. Field of the Invention
The present invention relates to a purification method and production method of 1-aminocyclopropanecarboxylic acid that is useful typically as an intermediate for fine chemicals such as pharmaceutical preparations and agricultural chemicals.
2. Description of the Related Art
1-Aminocyclopropanecarboxylic acid is useful typically as an intermediate for fine chemicals such as pharmaceutical preparations and agricultural chemicals and can be prepared by allowing 1-carbamoylcyclopropanecarboxylic acid to react with an aqueous sodium hydroxide solution and a bromine reagent (J. Am. Chem. Soc., 1984, 106, 5335-5348).
1-Aminocyclopropanecarboxylic acid is purified, for example, a purification method by ion-exchange column chromatography (J. Am. Chem. Soc., 1984, 106, 5335-5348); a method of mixing 1-aminocyclopropanecarboxylate hydrochloride with propylene oxide in ethanol solvent with stirring to thereby yield free 1-aminocyclopropanecarboxylic acid, concentrating the reaction mixture to dryness, and crystallizing the crude product from a mixture of water and acetone (J. Org. Chem., 1989, 1810-1815); a method of mixing 1-aminocyclopropanecarboxylate hydrochloride with potassium carbonate in methanol solvent with stirring to thereby yield free 1-aminocyclopropanecarboxylic acid, removing insoluble matter by filtration, concentrating the filtrate to dryness, and recrysltallizing the target compound from a mixture of ammonium hydroxide and ethanol (J. Org. Chem., 1990, 4276-4281); or a method of treating a reaction mixture containing 1-aminocyclopropanecarboxylic acid with hydrochloric acid, evaporating the treated reaction mixture to dryness, and extracting, with ethanol, the target compound as a hydrochloride from a mixture containing an inorganic salt (Japanese Unexamined Patent Application Publication No. 07-278077).
However, the method using ion-exchange column chromatography requires concentration of a large quantity of water, requires much time for separation, must be carried out using special devices and is not advantageous in industrial production. The method using propylene oxide is not industrially advantageous, since propylene oxide itself is very flammable, is spontaneously explosive and is hard to handle industrially. The method of crystallizing the target compound from a mixture of water and acetone cannot yield the target compound with high quality in a good yield, since the target compound 1-aminocyclopropanecarboxylic acid has a similar solubility to that of, if in coexistence, an inorganic salt such as sodium chloride or sodium bromide. The method of mixing 1-aminocyclopropanecarboxylate hydrochloride with potassium carbonate in methanol solvent with stirring to thereby yield free 1-aminocyclopropanecarboxylic acid, removing insoluble matter by filtration, concentrating the filtrate to dryness, and recrysltallizing the target compound from a mixture of ammonium hydroxide and ethanol is complicated in its procedure and is not industrially advantageous, since 1-aminocyclopropanecarboxylic acid is hardly soluble in methanol with a very low solubility of about 1.0% (wt/wt) and a large quantity of methanol is required. The method of extracting 1-aminocyclopropanecarboxylic acid as a hydrochloride with ethanol requires removal of hydrochloric acid before a subsequent process, which invites an increasing number of processes.